|

Top 5 Things To Do in Key West

Oh Key West, how I love you. This tiny island at the southern edge of the U.S. has so much to offer, I struggled to narrow this list down!

This Florida Key is the Southernmost point of the U.S. and is all the rage for the East-Coast Florida-bound (that is, if you aren’t into the Miami/ Tampa/ Panama City thing). It’s the party city for those of us who aren’t spring-breakers and works for a long weekend or long summer trip – whatever’s in the stars for you.

No matter how long you stay, here’s the top 5 must-do list for a trip to Key West.

You’ll also want to check this out – Key West Itinerary

* This post may contain affiliate links. If you click on one of them, we may receive a small commission (for which we are deeply grateful) at no extra cost to you. These affiliate links help support the future of whereversomeday.com. Your trust is everything to us, so rest assured that we only recommend products we know and trust.

Walk Duval

Okay, if you go to Key West and don’t check out Duval street, does it even count? I’d say no. At only around 4 miles wide, this island city is very much a walking city so I’d recommend not even renting a car and seeing the island with your own two shoes. While most streets are postcard-cute, everybody knows Duval is where the action is.

I’d recommend you head that way in the early evening, catch dinner, then stroll along Duval for the evening. If a bar hop is your thing, you’ll be in good company with plenty of great stops in the area.

Sunset Celebration at Mallory Square

Every night, people gather from all over the island for a few hours before sunset to watch the show. Through the busier summer months it’s even more of a to-do with music, entertainers and such.

You can grab a drink, listen to some music, and take in the view. Mallory Square is just down the street from Duval so you can start your evening there, and be close to the action on Duval after sunset.

Eat & Drink – DUH!

We can’t talk about any vacation without mentioning food and drinks! I’ve already mentioned the action on Duval street but let me just go ahead and say it – Key West is a party spot and there are endless watering holes to choose from.

For a stiff drink I recommend The Rum Bar on Duval. They make one hell of a Rum Runner, offer rum tours, and have a great low-key patio area to chill for the night.

For an INCREDIBLE dessert check out a restaurant called Better Than Sex. They just serve dessert and drinks but… I mean, what else do you need though?? You definitely need a reservation but the wait is well worth it for some out-of-this-world deliciousness. Served in a candle-lit romantic atmosphere with very-specific dessert names, this is ideal for couples without the kids for the night.

Considering the best route to your getaway in Key West? Check out our detailed guide to all your options – How to Get to Key West

Stay in a B&B

The B&B’s are the best thing about Key West (okay, fine, there are a lot of best things). For all the people who flock to Key West February – September, you’d think there’d be more mega-resorts, but it’s all about the Bed & Breakfasts here. Many are individually owned by locals and you’ll find they’re more passionate about Key West than any tourist in a rum bar.

I’ve most recently stayed with Authors of Key West Guesthouse, the most charming spot a bit removed from the main Duval hype.

There’s a ton of really great spots to stay and many include a full hot breakfast each morning and happy hour drinks each evening (score!). I would recommend you plan ahead, though. It’s not a big island and these places book up!

Yankee Freedom Dry Tortugas Day Trip

Seriously, please go on this trip. If you have only one day in Key West, spend it on this trip. It is pricey, but totally worth it. You’ll board the Yankee Freedom early in the morning and set sail for the Dry Tortugas, the most remote National Park in the U.S.

Breakfast and lunch are provided, and once you hit the island you can join a tour through Fort Jefferson or go scuba-diving off the pristine beach (equipment is provided). You’ll have plenty of time, so do it all!

This island and surrounding sea has very limited tourism, so you’ll see a ton in crystal clear water right in the beach area. Even sea turtles are known to stop through!


Ready to hit the road? Have you ever been to Key West? If so, tell me all about your favorite stops in the comments!

Join the Wherever Someday tribe!

Stop daydreaming and start planning.

Subscribe to receive exclusive travel tips that will help you make that “someday” trip a reality!

    Don’t worry, spam isn’t our thing. Unsubscribe at any time.

    Powered By ConvertKit